7 tips for hiring outside help on platforms like Freelancer.com

Online hiring

If you’re working solo or in a small team, you either do everything yourself or get help. If you’re getting help, then there are many options like volunteers or contractors. One common option is hiring from an online platform like or . There are many of these available.

I’m going to outline 7 of my top tips for hiring outside talent, via an online portal, from a pool of people you don’t already know.

I’ve used both and , and for most things, I prefer Upwork. I’ve used them regularly over the years, I recently went through three hiring processes for devs to help build a small tool (1 each). I was lucky enough to get two excellent hires and to cut short the other before money was involved.

Tip #1: Figure out what kind of manager you are.

Do you need more certainty about the assignment? Do you need to lock down the result, know in detail how it is going, or how much it will cost? Or are you happy to iterate your way towards the outcome?

Will poor English (or whatever your primary language) be problematic for you?

Nothing is either is right or wrong: the only bad thing is setting up an assignment in one mode when your mindset is the other.

Warning: be careful how “definite” you try to make things: all ideas evolve over their lifetimes. See Tip #2.

Tip #2: The first time you hire, go T&M and go small

With someone completely unknown, you should bootstrap yourselves into a working relationship over time.

You can iterate inside an assignment with small deliverables and milestones. And you can iterate over several tasks.

“T&M” = Time and Materials — basically you pay by the hour. Most platforms have a timesheeting tool that allows the person you hire to describe what they are doing.

I recommend not doing a Fixed Price assignment until at least the third assignment with the same person.

Tip #3: Make it easy to cull respondents to get a shortlist

Depending on the task, you could receive tens or even hundreds of “bids” on your job. You’re going to need to cull them somehow. I’ve tried various approaches with mixed success. my preferred one is to attach a document to the job when you post it. Call it a “scope description” or something.

Depending on your approach, you can make it as specific or open as you like. But make sure you do two things.

1) put in a specific question at the bottom that says “important: please answer this question in your bid response” and then ask something about the job: their approach, or how long they think it will take, for example.

2) put in your “pre-nup” wording. Then when you post the job, say something like, “Please read the scope description and ensure your proposal reflects the contents of that document.”

In my experience, 90% of respondents will give you canned responses which don’t reflect your specific requirements. They will say things like, “I can do everything you ask and more”, or “I’m fully qualified to do your job”, and so forth. So when it comes to culling, exclude anyone who obviously hasn’t read or understood your requirements.

Tip #4: Make sure you hire someone you can work with

No matter what the answer to #1 is, and no matter what you are building, the primary hiring criteria is that you two can work well together. The ability to work together sustainably is far more important than skills or hourly rate. Skills and money are essential factors but far less than working together and interacting in a positive and sustainable relationship.

You need to get a sense of how they respond to requests. I prefer to ask them to do something for me before I hire. For example, ask them to give you a very high-level breakdown of how they’d approach the task. Or describe something specific that they will do for you, given your particular situation. It almost doesn’t matter what you ask them for, and you’re checking how they react as much as what they provide.

Tip #5: Always set up a “pre-nup” or “kill switch.”

No matter how much you think you’ve done tip #2 well, risks are always involved. You need to gracefully (but rapidly) exit the arrangement if it’s not working for you or if you think the person is not thriving in the assignment. Make sure you set expectations about response times but be aware of timezone, work patterns and holidays. The job has to work for both parties and if it isn’t: kill it.

Ensure that the exit triggers are clearly defined and that you’ve discussed them with your prospective hire. Make sure they acknowledge and keep evidence. Some people will lodge complaints with the platform, and you need to be prepared to justify your actions.

See Tip #7 for more on this.

Tip #6: Be patient and respectful

These hiring platforms may result in gigs that are outside your experience. It’s likely that you’ll end up working with someone from a different culture and location. (refer to tip #1 — if this definitely isn’t going to work for you get that clear upfront).

Remote collaboration isn’t the best platform for starting with these relationships from scratch. But it’s what we get, especially in Covid times.

Both parties need to be flexible and allow for differences in culture and language. Be respectful. If someone doesn’t fully understand what you’re saying or asking, try to work through it another way.

Tip #7: Use the kill switch if need be.

Use it early — second chances are expensive if they don’t work. Use your intuition: is this likely to change? Avoid the “sunk cost” mentality. Be friendly but be firm. If they are worried about their platform reputation, be reasonable about how the termination affect them: have they been incompetent or dishonest? Or is it just not the right mix of people and jobs?

The Bottom Line

The assignment has to work for both parties: it’s great when it does, but don’t hesitate to step away if it isn’t working.

There are many other aspects of hiring outside help, for example, unpacking the volunteering pathway I mentioned above or dealing with the many pitfalls of the platforms.

Maybe I’ll do another post on them soon.

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